


adrift

by WattStalf



Series: Commissions [123]
Category: Original Work
Genre: F/M, Multi, Oral Sex, Polyamory, Sibling Incest, Underage Sex, Vaginal Sex
Language: English
Status: Completed
Published: 2020-06-09
Updated: 2020-06-09
Packaged: 2021-03-04 02:01:45
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,005
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24625924
Author URL: https://archiveofourown.org/users/WattStalf/pseuds/WattStalf
Summary: A brief look into the life of one older brother, his little sister, and her best friend that he has recently started dating.
Series: Commissions [123]
Series URL: https://archiveofourown.org/series/1325462
Kudos: 34





	adrift

Jake could not be prouder of himself right now. After making his plans to convince his parents, he thought that he would have to resort to a lot more begging, maybe even bribery, to get them to let him take their yacht out while staying at their Monaco villa, but in the end, they were just as excited by the idea as he was. Of course, now that he thinks about it, it becomes pretty apparent why, and he realizes that he has already done his part, contributed his payment for their kindness.

They could not be any more thrilled at his choice of girlfriend, after all. His father and Katie’s father have been business partners for as far back as he can remember, and they were probably hoping that the two of them would eventually fall in love and unite the two families. The fact that Katie is three years younger than him does not seem to be much of an issue, and even her father is happy for them, claiming that his little girl is mature enough to handle Jake, and that, if there is any boy in the world he could trust with her, it would be his partner’s son.

The issue of their age gap would not seem like an issue at all, once they had both grown up a little, he was quickly assured, not that he ever had any concern with it. And with his eighteenth birthday on the horizon, this had seemed like the perfect way to celebrate. His parents must have thought that it would only serve to further endear Katie to him, and were eager to let them go, without making him really have to beg for it.

They only had one condition to their offer- he had to take his little sister, Jennifer, with the two of them. That was likely to help ensure that Katie wasn’t  _ too _ endeared by it all, as if Jen could serve as some sort of chaperone, but also in the interest of being fair, and not letting their oldest child have all the fun, just because it was his birthday.

But that does not put a damper on any of Jake’s plans. Though he does not mention it to his parents, not wanting them to think that he is getting off too easy, he had already been planning to bring Jen from the beginning. She is Katie’s best friend, for one thing, and, not only that, but the two of them have always been close, perhaps a bit too close for siblings. All three of them grew up together, so it just wouldn’t seem right to leave Jen behind.

These things are better kept to themselves, much like their past together, a love triangle that might be a bit too amicable to really describe as a triangle. Katie seems to have no issues with how close Jake and Jen are, actively encouraging them to be together, while also treating Jake as if he is her own brother. With how close she is to the family, he might as well be, but now that they are dating, it seems a little odd for her to openly call him “bro,” so she sticks to doing that in private.

In private, the three of them have a very different dynamic than that of an older brother dating his younger sister’s best friend. With Katie encouraging their incestuous affair while doing everything she can to be a part of it, there is just no way they could leave Jen out of their little trip, but he acts as if he is taking on a sacrifice by inviting her along as well. Everything goes perfectly to plan, and Jake could not be more proud of himself for ending up here.

Even with their attempts to send Jen along to make sure that he and Katie are not completely alone, he is sure that his parents must suspect that the two of them will find time to be alone, fucking every night that they have the chance, and they would not be wrong in that assumption. In the back of their minds, they must be secretly hoping for that as well, even if, as responsible parents, they might feel like they should discourage that kind of behavior.

If she were to get pregnant, that would pretty much cement the marriage that they are hoping for, even if she is currently too young for such a thing. With her parents permission, things could be done about it, or, at the very least, she would be promised to him after she was old enough, finally uniting their families. On the one hand, they feel responsible for keeping the kids from going too far, but on the other hand, they stand to benefit quite a bit if they do.

Jake is certainly hoping for that outcome as well, though not for the reasons that they are. He could not care less about the business side of their family’s relationships, and he doubts that Katie cares much about that either. But she  _ does _ want to leave this vacation knocked up, and he is doing everything in his power to make sure that that happens, knowing already that they will not have to face real consequences from either of their families.

The boat has been anchored, and the smooth waters of the ocean leave the boat gently bouncing on the water. This afternoon is absolutely perfect, and he relaxes, so proud of himself for getting the three of them into this situation, and so excited for what is to come, certain that they have done a good job carrying out those plans so far.

Jen is on her knees before him, planting kisses all over his cock, whimpering and moaning as she does. She and Katie had already planned this out before they even planned the trip, deciding that they would present themselves to him as his birthday present this year, and though he has spent a lot of time with Katie, trying to make sure that he impregnates her, right now it is Jen’s turn.

He runs a hand through her hair as she runs her tongue up and down his cock in between kisses, sighing happily, before he pushes her head forward, and then pulls her head down on his cock, filling her mouth to put an end to her teasing. Jake moans happily, and Jen whimpers, looking up at him with bright and loving eyes. She is his birthday present just as much as his girlfriend is, but the three of them have always done everything together, just like this.

Katie is above deck right now, so for now, the two of them are just warming up. Jen was teasing him with her mouth, and now he makes her go all the way with it, though he has no intention of finishing in her mouth. He will wait until Katie comes back down to join them before he lets himself finish, and when he does, he will be buried inside of his sister, filling her with every last drop of his seed.

The goal for their vacation is not just to ensure that Katie is impregnated, but his little sister as well. Both girls are fortunate enough to be at their most fertile right now, on the same cycle because they have spent so much time together, or so believe. When they calculated things out, and realized that would coincide with his birthday, that is when they began planning to give themselves to him, wanting this to be when he impregnates both of them at the same time.

The best friends are absolutely gorgeous, a real force to be reckoned with even at the age of fourteen. And despite their age, they are both filled out, with enviable curves that give their bodies an edge of maturity that their young faces deny. Together, they are more than any man could hope to resist, and Jake was powerless from the start, not that he minds the position that he is in, especially not right now, with his little sister’s head bobbing on his cock.

Groaning in contentment, he says, “This is seriously the best birthday ever. You guys have outdone yourselves, you know that?” Jen hums happily in response, pleased to hear the way her brother praises her for her efforts, and so turned on right now that she can hardly stand it. She has had the chance to watch her brother with Katie during their trip, so that has only helped to build up the anticipation for her own turn with him.

His hand remains firm on the back of her head while she sucks him off, both of them waiting for Katie to return below deck so that they can properly get started. For Jake, it becomes difficult to hold back with how good of a job his little sister is doing, and for Jen, it the best sort of torture imaginable, waiting for her older brother to finally fill her, while her best friend and soon-to-be sister watches.

“Did you two get started without me?” a voice calls out, and soon enough, Katie comes into sight, descending with a smile on her face.

“As if we would,” he replies, his voice showing signs of strain as he fights back against his own pleasure. “We were just getting warmed up while we waited for you, of course.”

Her smile only grows as she says, “Well, you don’t have to wait anymore, bro! Sorry if I kept you waiting for too long.”

Jen comes up for air then, her mouth creating a soft pop as she does, and she grins over at Katie. “Yeah, well, enjoy the show. It’s finally my turn to get knocked up!”

Katie takes a seat across from the two of them, where she has a good view as Jen stands up, shifting their position so that she can straddle Jake. He plants his hands on her hips, pulling her down to sink onto his cock, the two of them groaning in unison, the relief almost more than they can stand.

After all the work she did to get him warmed up, it’s no surprise that it does not take him very long to come, filling her with a soft moan, but neither of them are done with each other just yet. Jen just keeps bouncing on top of him, not wanting to lose a bit of momentum, and not wanting to waste a moment. She plans to milk him completely dry tonight, until he has given her everything that he has, to make sure that she leaves this vacation pregnant, just the same as Katie. Between the two of them, he knows he will be completely worn out by the time it is all over, but that exhaustion will be more than worth it, in the end.

~X~

Before Jen even begins showing signs of her pregnancy, his parents have already figured things out. He has no idea how they managed to discover that the real reason he was so willing to bring his little sister along for the ride is because the two of them are fucking, but they did, and he expects some kind of punishment.

Instead, he is offered a deal: just as long as he stays with Katie and keeps Katie happy, as long as he offers Katie the same happiness that he does his sister, and as long as he has children with Katie, then they will help him keep that affair going as well. After all, if Katie is happy sharing her boyfriend with her best friend, then there is no real need to put an end to things, is there?

At the end of the day, his parents care only for the financial benefits that come from his relationship with Katie. If all three of them can be happy together, then keeping the incestuous side of things a secret is more than worth the effort.

**Author's Note:**

> If you're interested in my writing updates, please follow my fanfiction twitter @WattStalf  
> 


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